16 Best Vacation Dresses 2023

Every item on this page was chosen by a The Pioneer Woman editor. We may earn commission on some of the items you choose to buy.

Editor’s Pick

The Ellie Nap Dress

The Ellie Nap Dress

Editor’s Pick

The Ellie Nap Dress

Credit: Hill House Home

No list of summery dresses would be complete without the super popular Nap Dress. The smocked bodice will feel ultra comfortable while the fluttery sleeves give it such style. And that classic blue and white stripe pattern? Why, it has all the nautical vibes!

$20 Find

Boho Long Maxi Sundress

Boho Long Maxi Sundress

$20 Find

Boho Long Maxi Sundress

Credit: Walmart

This palm leaf print dress will have you feeling like you’re in paradise… especially since it’s only $20! We love the flattering halter neckline and cute bow that cinches at the waist.

Taste of the Tropics

Hilo Wrap Dress

Hilo Wrap Dress

Taste of the Tropics

Hilo Wrap Dress

Credit: Everything But Water

Feel like you’re in Hawaii whether you are or not with this tropical print pick. The adjustable tie waist keeps it comfortable and the wrap style will look flattering on anyone.

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Extended Sizes

Halter Maxi Dress

Halter Maxi Dress

Extended Sizes

Halter Maxi Dress

Credit: Gap

If super vibrant colors aren’t your vibe, look pretty in pastels! This tiered halter dress has a loose but flattering fit and hits right above the ankle―on anyone! It comes in petite, regular, and tall sizes.

Best Wrap Dress

Floral Wrap Dress

Floral Wrap Dress

Best Wrap Dress

Floral Wrap Dress

Now 23% Off

Credit: Amazon

Wrap dresses are always so flattering and feminine. Add in flowy flutter sleeves and you’ve got yourself an even bigger winner! There are over 30 pretty prints and solid colors to choose from, too.

Bestseller

The Somerset Maxi Dress

The Somerset Maxi Dress

Bestseller

The Somerset Maxi Dress

Credit: Anthropologie

If you haven’t purchased The Somerset dress yet, we think now is the time! It is the most reviewed dress from Anthropologie ever, and this new print is one of the best there is. It comes in petite and plus sizes, too!

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5-Star Reviews

Maren Midi Dress in Wildflower Bouquet

Maren Midi Dress in Wildflower Bouquet

5-Star Reviews

Maren Midi Dress in Wildflower Bouquet

Credit: Draper James

With a trendy square neckline and midi hem, this dress will have you looking perfectly in style while vacationing. And while we adore the floral print, our favorite part is the subtle dot texture on the fabric.

Pretty in Pink

Gathered V-Neck Maxi Dress

Gathered V-Neck Maxi Dress

Pretty in Pink

Gathered V-Neck Maxi Dress

Credit: Boden

You don’t necessarily need a print to feel that vacation vibe. A bright color like this stunning pink will do the trick! The relaxed fit and super flowy fabric will keep you comfortable and confident in the heat, too.

Flowy Style

Print Kimono Maxi Dress

Print Kimono Maxi Dress

Flowy Style

Print Kimono Maxi Dress

Now 17% Off

Credit: Amazon

Long live the comfy kimono-inspired dress! It offers a loose fit where you want it but stays flattering thanks to the cinching at the waist. We love the flowy ocean feel of this pastel print, but there are over 30 other options to choose from if you want something else.

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Ready for the 4th

Americana Stripe Short Sleeve Gio Maxi Dress

Americana Stripe Short Sleeve Gio Maxi Dress

Ready for the 4th

Americana Stripe Short Sleeve Gio Maxi Dress

Credit: Tuckernuck

Red, white, and blue stripes are perfect for all those summer holidays, even if you’re not in the good ol’ USA. The comfy T-shirt look is a classic that you can wear anywhere, too.

Super Soft Fabric

Multi Palm Sleeveless Tiered Maxi Dress

Multi Palm Sleeveless Tiered Maxi Dress

Super Soft Fabric

Multi Palm Sleeveless Tiered Maxi Dress

Now 59% Off

Credit: Lands’ End

Soft jersey fabric, a flattering tiered skirt, and a perfectly seasonal print―this dress has all the makings of a vacation dress, for sure. Check out the six other color options, too! They are all totally different and totally fun.

Best Vintage-Inspired

Linen-Blend Tie-Back Tiered Maxi Dress

Linen-Blend Tie-Back Tiered Maxi Dress

Best Vintage-Inspired

Linen-Blend Tie-Back Tiered Maxi Dress

Credit: Gap

This vintage-inspired cutie is equal parts retro and modern, and the linen blend fabric is just perfect for warm weather. It’s available in regular and tall sizes, too, depending on where you want the hem to hit.

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Adjustable Fit

Short Sleeve Loose Maxi Dresses

Short Sleeve Loose Maxi Dresses

Adjustable Fit

Short Sleeve Loose Maxi Dresses

Now 22% Off

Credit: Amazon

Our favorite part of this dress is the tie waist. You can cinch it for a fitted look or wear it loose for a more flowy style. The tropical print is perfect, too, but if you want something else, check out the other 10+ options.

Transitional Colors

Twist Front Maxi Cami Maxi Dress

Twist Front Maxi Cami Maxi Dress

Transitional Colors

Twist Front Maxi Cami Maxi Dress

Credit: Boden

This tie-front silhouette is not only super flattering but also perfect for a day on the beach. We love that the colors are fall-friendly, too. Just pop on a sweater and some boots!

40+ Prints

Tie-Dye Sleeveless Maxi Dress

Tie-Dye Sleeveless Maxi Dress

40+ Prints

Tie-Dye Sleeveless Maxi Dress

Credit: Amazon

Even though we love prints, sometimes you just need a little tie dye in your life. And vacation is the time to do it! This casual cotton blend maxi has pockets, and it comes in dozens of pattern and color options.

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Indigo Wave Joey Maxi Dress

Indigo Wave Joey Maxi Dress

Indigo Wave Joey Maxi Dress

Credit: Wolf & Badger

This abstract print is reminiscent of beachy waves without being too on-the-nose. We love the drapy look that’s equal parts casual and dressy at the same time. It would look just as good with a pair of flip-flops as it would with strappy heels!

Headshot of AnnMarie Mattila

Commerce Editor

AnnMarie Mattila is the Commerce Editor for The Pioneer Woman, covering products ranging from home, fashion, beauty, and more. 

Headshot of Belle Bakst

Belle Bakst is a fashion market assistant for BAZAAR. When she’s not in the office you can find her at Bergdorf Goodman, or thrifting in Chelsea. She can virtually always be seen with a coffee in hand. Follow her on instagram @littlefashionstylist. 

 

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